DE594275C - Process for the production of glycine from its esters and their salts by saponification - Google Patents

Process for the production of glycine from its esters and their salts by saponification

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Publication number
DE594275C
DE594275C DEG83947D DEG0083947D DE594275C DE 594275 C DE594275 C DE 594275C DE G83947 D DEG83947 D DE G83947D DE G0083947 D DEG0083947 D DE G0083947D DE 594275 C DE594275 C DE 594275C
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Germany
Prior art keywords
saponification
glycine
salts
esters
ester
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
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DEG83947D
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German (de)
Inventor
Dr Wilhelm Gluud
Dr Hans Joachim Riedl
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gesellschaft fuer Kohlentechnik mbH
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Gesellschaft fuer Kohlentechnik mbH
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Publication date
Application filed by Gesellschaft fuer Kohlentechnik mbH filed Critical Gesellschaft fuer Kohlentechnik mbH
Priority to DEG83947D priority Critical patent/DE594275C/en
Application granted granted Critical
Publication of DE594275C publication Critical patent/DE594275C/en
Expired legal-status Critical Current

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Description

Verfahren zur Gewinnung von Glycin aus seinen Estern und deren Salzen durch Verseifung Die Darstellung der Aminoesgigsäure führt in vielen Fällen über ihre Ester als Zwischenprodukte. So erhält man beispielsweise bei der Reduktion von Cyanameisensäureester mittels Wasserstoffs den entsprechenden .4minoessigsäureester, aus welchem durch Verseifen das freie Glycin erhalten wird. Bei dieser Operation ergibt sich die Schwierigkeit, daß, zufolge der Neigung des freien Glycinesters in sogenannte Biuretbase oder Diketopiperacin überzugehen, eine Verseifung mit Wasser allein nicht zu reinen Produkten führt. Vollzieht man dagegen die Verseifung in Anwesenheit von Mineralsäuren oder Alkalien, so erhält man in ersterem Falle mineralsaures Glycin, z. B. sein Chlorhydrat, im letzteren Falle die Alkalisalze des Glycins, z. B. aminoessigsaures Natrium. Will man aus diesen Verbindungen das Glycin in Freiheit setzen, so erfordert dies wiederum eine Nachbehandlung, im ersteren Falle mit Al- kali, im letzteren mit Säure, so daß man stets als Endergebnis ein Gemisch von freiem Glycin und Alkalisalz erhält, deren Trennung schwierig ist.Process for the production of glycine from its esters and their salts by saponification The preparation of the aminoesgetic acid leads in many cases via its esters as intermediate products. For example, when cyanoformate is reduced by means of hydrogen, the corresponding .4minoacetic ester is obtained, from which the free glycine is obtained by saponification. This operation has the problem that, due to the tendency of the free glycine ester to convert into so-called biuret base or diketopiperacin, saponification with water alone does not lead to pure products. If, on the other hand, the saponification is carried out in the presence of mineral acids or alkalis, then in the former case mineral acid glycine, e.g. B. its hydrochloride, in the latter case the alkali salts of glycine, z. B. Sodium aminoacetate. One wants from these compounds release the glycine in freedom, this in turn requires a post-treatment, in the former case with Al kali, in the latter with acid, so that always obtained as a final result, a mixture of free glycine, and alkali metal salt, the separation of which is difficult .

Es wurde nun gefunden, daß sich die Verseifung des Glycinesters ohne die Bildung organischer und anorganischer Nebenprodukte durchführen läßt, wenn man sie in Anwesenheit von Essigsäure vornimmt. Liegt der Glycinester in Form eines seiner Salze, z. B. des Chlorhydrats, vor, so ist der Säurebestandteil (HCl) vorher zu entfernen. Es geschieht dies zweckmäßig dadurch, daß man die alkoholische Lösung des Esterchlorhydrats zwecks Abspaltung der Salzsäure mit der berechneten Menge starker Natronlauge versetzt und das entstandene Kochsalz abfiltriert. Das alkoholische Filtrat wird mit mäßig verdünnter Essigsäure versetzt, der Alkohol abdestilliert, die essigsaure Lösung durch Kochen in 5 bis ro Stunden völlig verseift und dann zur Trockne eingedampft. Es hinterbleibt ein sehr reines Glycin, das von den obengenannten organischen Verunreinigungen frei ist -- ein beständiges Acetat vermag es nicht zu bilden - und höchstens noch geringe Mengen Kochsalz enthält. Wendet man das Natron in Form eines Alkoholates an, arbeitet man also in völliger Abwesenheit von Wasser und so, daß sich auch während der .Abspaltung der Säure kein solches bilden kann, so läßt sich erforderlichenfalls der Kochsalzgehalt des Glycins noch weiter herabsetzen.It has now been found that the saponification of the glycine ester without the formation of organic and inorganic by-products can be carried out if does it in the presence of acetic acid. If the glycine ester is in the form of a its salts, e.g. B. the hydrochloric acid before, the acid component (HCl) is before to remove. This is conveniently done by adding the alcoholic solution of the ester chlorohydrate for the purpose of splitting off the hydrochloric acid with the calculated amount strong sodium hydroxide solution and the resulting sodium chloride filtered off. The alcoholic Slightly dilute acetic acid is added to the filtrate, the alcohol is distilled off, the acetic acid solution is completely saponified by boiling in 5 to ro hours and then evaporated to dryness. What remains is a very pure glycine, that of the above is free of organic impurities - a permanent acetate cannot to form - and contains no more than small amounts of table salt. If you turn the baking soda in the form of an alcoholate, so one works in the complete absence of water and in such a way that no acid can form even during the splitting off of the acid, in this way, if necessary, the salt content of the glycine can be reduced even further.

Claims (1)

PATENTANSPRÜCHE: z. Verfahren zur Gewinnung von Glycin aus seinen Estern und "deren Salzen durch Verseifung, dadurch gekennzeichnet, daß man die Verseifung des Esters mit organischen Säuren, wie Essigsäure o. dgl., vornimmt und das freie Gly'cin durch Abdampfen des Reaktionsgemisches zur Trockne als Rückstand gewinnt. a. Verfahren nach Anspruch i, dadurch gekennzeichnet, daß man bei Vorliegen des Esters in Form eines seiner Salze vor der eigentlichen V erseifung den Säurebestandteil in Salzform entfernt.PATENT CLAIMS: e.g. Process for obtaining glycine from its Esters and "their salts by saponification, characterized in that man the saponification of the ester with organic acids such as acetic acid or the like and the free gly'cine as a residue by evaporating the reaction mixture to dryness wins. a. Process according to Claim i, characterized in that, when present of the ester in the form of one of its salts, before the actual saponification, the acid component removed in salt form.
DEG83947D 1932-11-01 1932-11-01 Process for the production of glycine from its esters and their salts by saponification Expired DE594275C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEG83947D DE594275C (en) 1932-11-01 1932-11-01 Process for the production of glycine from its esters and their salts by saponification

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEG83947D DE594275C (en) 1932-11-01 1932-11-01 Process for the production of glycine from its esters and their salts by saponification

Publications (1)

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DE594275C true DE594275C (en) 1934-03-14

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DEG83947D Expired DE594275C (en) 1932-11-01 1932-11-01 Process for the production of glycine from its esters and their salts by saponification

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2642459A (en) * 1948-12-08 1953-06-16 Dow Chemical Co Production and purification of amino acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2642459A (en) * 1948-12-08 1953-06-16 Dow Chemical Co Production and purification of amino acids

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